EP2999021B1 - Phosphoreszierende materialien - Google Patents

Phosphoreszierende materialien Download PDF

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EP2999021B1
EP2999021B1 EP15191449.6A EP15191449A EP2999021B1 EP 2999021 B1 EP2999021 B1 EP 2999021B1 EP 15191449 A EP15191449 A EP 15191449A EP 2999021 B1 EP2999021 B1 EP 2999021B1
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compound
product
reaction mixture
organic
materials
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EP2999021A1 (de
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Bert Alleyne
Raymond Kwong
Walter Yeager
Chuanjun Xia
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Universal Display Corp
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Universal Display Corp
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/10—Transparent electrodes, e.g. using graphene
    • H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
    • H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/805—Electrodes
    • H10K50/81—Anodes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/805—Electrodes
    • H10K50/82—Cathodes

Definitions

  • the claimed invention was made by, on behalf of, and/or in connection with one or more of the following parties to a joint university corporation research agreement: Regents of the University of Michigan, Princeton University, The University of Southern California, and the Universal Display Corporation. The agreement was in effect on and before the date the claimed invention was made, and the claimed invention was made as a result of activities undertaken within the scope of the agreement.
  • the present invention relates to organic light emitting devices (OLEDs), and specifically to phosphorescent organic materials used in such devices. More specifically, the present invention relates to iridium compounds having a narrow spectrum incorporated into OLEDs.
  • Opto-electronic devices that make use of organic materials are becoming increasingly desirable for a number of reasons. Many of the materials used to make such devices are relatively inexpensive, so organic opto-electronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications such as fabrication on a flexible substrate. Examples of organic opto-electronic devices include organic light emitting devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, the organic materials may have performance advantages over conventional materials. For example, the wavelength at which an organic emissive layer emits light may generally be readily tuned with appropriate dopants.
  • OLEDs organic light emitting devices
  • the wavelength at which an organic emissive layer emits light may generally be readily tuned with appropriate dopants.
  • OLEDs make use of thin organic films that emit light when voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, illumination, and backlighting. Several OLED materials and configurations are described in U.S. Pat. Nos. 5,844,363 , 6,303,238 , and 5,707,745 .
  • phosphorescent emissive molecules is a full color display.
  • Industry standards for such a display call for pixels adapted to emit particular colors, referred to as "saturated" colors.
  • these standards call for saturated red, green, and blue pixels. Color may be measured using CIE coordinates, which are well known to the art.
  • a green emissive molecule is tris(2-phenylpyridine) iridium, denoted Ir(ppy) 3 , which has the structure of Formula I:
  • organic includes polymeric materials as well as small molecule organic materials that may be used to fabricate organic opto-electronic devices.
  • Small molecule refers to any organic material that is not a polymer, and "small molecules” may actually be quite large. Small molecules may include repeat units in some circumstances. For example, using a long chain alkyl group as a substituent does not remove a molecule from the "small molecule” class. Small molecules may also be incorporated into polymers, for example as a pendent group on a polymer backbone or as a part of the backbone. Small molecules may also serve as the core moiety of a dendrimer, which consists of a series of chemical shells built on the core moiety.
  • the core moiety of a dendrimer may be a fluorescent or phosphorescent small molecule emitter.
  • a dendrimer may be a "small molecule,” and it is believed that all dendrimers currently used in the field of OLEDs are small molecules.
  • top means furthest away from the substrate, while “bottom” means closest to the substrate.
  • first layer is described as “disposed over” a second layer, the first layer is disposed further away from substrate. There may be other layers between the first and second layer, unless it is specified that the first layer is "in contact with” the second layer.
  • a cathode may be described as “disposed over” an anode, even though there are various organic layers in between.
  • solution processible means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium, either in solution or suspension form.
  • a ligand may be referred to as "photoactive” when it is believed that the ligand directly contributes to the photoactive properties of an emissive material.
  • a ligand may be referred to as "ancillary” when it is believed that the ligand does not contribute to the photoactive properties of an emissive material, although an ancillary ligand may alter the properties of a photoactive ligand.
  • a first "Highest Occupied Molecular Orbital” (HOMO) or “Lowest Unoccupied Molecular Orbital” (LUMO) energy level is “greater than” or "higher than” a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level.
  • IP ionization potentials
  • a higher HOMO energy level corresponds to an IP having a smaller absolute value (an IP that is less negative).
  • a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (an EA that is less negative).
  • the LUMO energy level of a material is higher than the HOMO energy level of the same material.
  • a "higher” HOMO or LUMO energy level appears closer to the top of such a diagram than a "lower” HOMO or LUMO energy level.
  • a first work function is "greater than” or “higher than” a second work function if the first work function has a higher absolute value. Because work functions are generally measured as negative numbers relative to vacuum level, this means that a "higher” work function is more negative. On a conventional energy level diagram, with the vacuum level at the top, a “higher” work function is illustrated as further away from the vacuum level in the downward direction. Thus, the definitions of HOMO and LUMO energy levels follow a different convention than work functions.
  • An organic light emitting device comprises an anode, a cathode, and an organic layer disposed between the anode and the cathode.
  • the organic layer comprises one or more of the inventive compounds.
  • the organic layer can be an emissive layer that contains an emissive dopant and a host, wherein the inventive compound is the emissive dopant and BAlq is the host.
  • a consumer product comprises a device which itself comprises an anode, a cathode, and an organic layer disposed between the anode and the cathode.
  • the organic layer comprises one or more of the inventive compounds.
  • organometallic compound is also provided, the organometallic compound containing a structure selected from the group consisting of: wherein M is a metal with an atom weight greater than 40.
  • an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode.
  • the anode injects holes and the cathode injects electrons into the organic layer(s).
  • the injected holes and electrons each migrate toward the oppositely charged electrode.
  • an "exciton” which is a localized electron-hole pair having an excited energy state, is formed.
  • Light is emitted when the exciton relaxes via a photoemissive mechanism.
  • the exciton may be localized on an excimer or an exciplex. Non-radiative mechanisms, such as thermal relaxation, may also occur, but are generally considered undesirable.
  • the initial OLEDs used emissive molecules that emitted light from their singlet states ("fluorescence") as disclosed, for example, in U.S. Pat. No. 4,769,292 . Fluorescent emission generally occurs in a time frame of less than 10 nanoseconds.
  • FIG. 1 shows an organic light emitting device 100.
  • Device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emissive layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, and a cathode 160.
  • Cathode 160 is a compound cathode having a first conductive layer 162 and a second conductive layer 164.
  • Device 100 may be fabricated by depositing the layers described, in order. The properties and functions of these various layers, as well as example materials, are described in more detail in US 7,279,704 at cols. 6-10.
  • a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363 .
  • An example of a p-doped hole transport layer is m-MTDATA doped with F.sub.4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980 .
  • Examples of emissive and host materials are disclosed in U.S. Pat. No. 6,303,238 to Thompson et al.
  • An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980 .
  • U.S. Pat. Nos. 5,703,436 and 5,707,745 disclose examples of cathodes including compound cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, electrically-conductive, sputter-deposited ITO layer.
  • the theory and use of blocking layers is described in more detail in U.S. Pat. No. 6,097,147 and U.S. Patent Application Publication No. 2003/0230980 .
  • Examples of injection layers are provided in U.S. Patent Application Publication No. 2004/0174116 .
  • a description of protective layers may be found in U.S. Patent Application Publication No. 2004/0174116 .
  • FIG. 2 shows an inverted OLED 200.
  • the device includes a substrate 210, a cathode 215, an emissive layer 220, a hole transport layer 225, and an anode 230.
  • Device 200 may be fabricated by depositing the layers described, in order. Because the most common OLED configuration has a cathode disposed over the anode, and device 200 has cathode 215 disposed under anode 230, device 200 may be referred to as an "inverted" OLED. Materials similar to those described with respect to device 100 may be used in the corresponding layers of device 200.
  • FIG. 2 provides one example of how some layers may be omitted from the structure of device 100.
  • FIGS. 1 and 2 The simple layered structure illustrated in FIGS. 1 and 2 is provided by way of non-limiting example, and it is understood that embodiments of the invention may be used in connection with a wide variety of other structures.
  • the specific materials and structures described are exemplary in nature, and other materials and structures may be used.
  • Functional OLEDs may be achieved by combining the various layers described in different ways, or layers may be omitted entirely, based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe various layers as comprising a single material, it is understood that combinations of materials, such as a mixture of host and dopant, or more generally a mixture, may be used. Also, the layers may have various sublayers.
  • hole transport layer 225 transports holes and injects holes into emissive layer 220, and may be described as a hole transport layer or a hole injection layer.
  • an OLED may be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials as described, for example, with respect to FIGS. 1 and 2 .
  • OLEDs comprised of polymeric materials (PLEDs) such as disclosed in U.S. Pat. No. 5,247,190 to Friend et al.
  • PLEDs polymeric materials
  • OLEDs having a single organic layer may be used.
  • OLEDs may be stacked, for example as described in U.S. Pat. No. 5,707,745 to Forrest et al.
  • the OLED structure may deviate from the simple layered structure illustrated in FIGS. 1 and 2 .
  • the substrate may include an angled reflective surface to improve out-coupling, such as a mesa structure as described in U.S. Pat. No. 6,091,195 to Forrest et al. , and/or a pit structure as described in U.S. Pat. No. 5,834,893 to Bulovic et al.
  • any of the layers of the various embodiments may be deposited by any suitable method.
  • preferred methods include thermal evaporation, ink-jet, such as described in U.S. Pat. Nos. 6,013,982 and 6,087,196 , organic vapor phase deposition (OVPD), such as described in U.S. Pat. No. 6,337,102 to Forrest et al. , and deposition by organic vapor jet printing (OVJP), such as described in U.S. patent application Ser. No. 10/233,470 .
  • OVPD organic vapor phase deposition
  • OJP organic vapor jet printing
  • Other suitable deposition methods include spin coating and other solution based processes. Solution based processes are preferably carried out in nitrogen or an inert atmosphere.
  • preferred methods include thermal evaporation.
  • Preferred patterning methods include deposition through a mask, cold welding such as described in U.S. Pat. Nos. 6,294,398 and 6,468,819 and patterning associated with some of the deposition methods such as ink-jet and OVJD. Other methods may also be used.
  • the materials to be deposited may be modified to make them compatible with a particular deposition method.
  • substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing. Substituents having 20 carbons or more may be used, and 3-20 carbons is a preferred range. Materials with asymmetric structures may have better solution processibility than those having symmetric structures, because asymmetric materials may have a lower tendency to recrystallize. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.
  • Devices fabricated in accordance with embodiments of the invention may be incorporated into a wide variety of consumer products, including flat panel displays, computer monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads up displays, fully transparent displays, flexible displays, laser printers, telephones, cell phones, personal digital assistants (PDAs), laptop computers, digital cameras, camcorders, viewfinders, micro-displays, vehicles, a large area wall, theater or stadium screen, or a sign.
  • PDAs personal digital assistants
  • Various control mechanisms may be used to control devices fabricated in accordance with the present invention, including passive matrix and active matrix. Many of the devices are intended for use in a temperature range comfortable to humans, such as 18 degrees C. to 30 degrees C., and more preferably at room temperature (20-25 degrees C.).
  • the materials and structures described herein may have applications in devices other than OLEDs.
  • other optoelectronic devices such as organic solar cells and organic photodetectors may employ the materials and structures.
  • organic devices such as organic transistors, may employ the materials and structures.
  • halo, halogen, alkyl, cycloalkyl, alkenyl, alkynyl, arylkyl, heterocyclic group, aryl, aromatic group, and heteroaryl are known to the art, and are defined in US 7,279,704 at cols. 31-32.
  • Ir(2-phenylquinoline) and Ir(1-phenylisoquinoline) type phosphorescent materials have been synthesized, and OLEDs incorporating them as the dopant emitters have been fabricated.
  • the devices may exhibit advantageously exhibit high current efficiency, high stability, narrow emission, improved processibility (e.g., high solubility and low sublimation temperature), and/or high luminous efficiency: quantum efficiency ratio (LE:EQE).
  • Ir(3-Meppy)3 as a base structure, different alkyl substitution patterns on both the emitting ligand and the ancillary ligand were studied to establish a structure-property relationship with respect to material processibility (evaporation temperature, evaporation stability, solubility, etc) and device characteristics of Ir(2-phenylquinoline) and Ir(1-phenylisoquinoline) type phosphorescent materials and their PHOLEDs.
  • Alkyl substitutions are particularly important because they offer a wide range of tunability in terms of evaporation temperature, solubility, energy levels, device efficiency and narrowness of the emission spectrum. Moreover, they are stable functional groups chemically and in device operation when applied appropriately.
  • the compounds described herein provide high device efficiency and stability, and a very narrow spectrum among other desirable properties. It is thought that a branched substituents at least at one of R x and R y , in combination with the methyl substituents on the phenyl ring (ring B) of the compound may provide for the very narrow emission spectrum and other remarkably good properties of the compound.
  • An organic light emitting device comprises an anode, a cathode, and an organic layer that is disposed between the anode and the cathode.
  • the organic layer further comprising a compound as defined by claim 5.
  • the organic layer of the device is an emissive layer comprising the compound and a host.
  • the compound is the emissive material.
  • the host is a metal coordination complex.
  • the host material can be BAlq.
  • the compound of the device is the emissive material and the host is a metal coordination complex.
  • the host material can be BAlq.
  • an organic light emitting device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound selected from the group consisting of:
  • the organic later of the device can be an emissive layer comprising the compound and a host.
  • the inventive compound can be the emissive material and the host can be a metal coordination complex.
  • the host can be BAlq.
  • a consumer product comprising a device, the device further comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode.
  • the organic layer further comprising a compound as defined in claim 1.
  • the consumer product comprises a device, the device further comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode.
  • the organic layer further comprising a compound selected from the group consisting of:
  • the method can further comprise reacting with a metal M and one or more ligands to form a compound having the formula: wherein M is a metal of atomic weight higher than 40; wherein A and B are each independently a 5 or 6-membered aromatic or heteroaromatic ring, and A-B represents a bonded pair of aromatic or heteroaromatic rings coordinated to the metal via a nitrogen atom on ring A and an sp 2 hybridized carbon atom on ring B; wherein R A and R B each represent no substitution or one or more substituents; wherein each substituent of R A and R B is independently selected from the group consisting of alkyl, heteroalkyl, aryl, or heteroaryl groups; wherein m is the oxidation state of the metal; and wherein n is an integer less than m and at least 1.
  • the method can further comprise wherein R z is a methyl group; and wherein
  • Isotopic analogues of the compounds provided herein where hydrogen has been replaced by deuterium are also included.
  • organometallic compound contains a structure selected from the group consisting of wherein M is a metal with an atomic weight greater than 40.
  • the organometallic compound provided can have M as Ir.
  • the organometallic compound provided can be a phosphorescent material.
  • the materials described herein as useful for a particular layer in an organic light emitting device may be used in combination with a wide variety of other materials present in the device.
  • emissive dopants disclosed herein may be used in conjunction with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes and other layers that may be present.
  • the materials described or referred to below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that may be useful in combination.
  • hole injection materials In addition to and / or in combination with the materials disclosed herein, many hole injection materials, hole transporting materials, host materials, dopant materials, exiton/hole blocking layer materials, electron transporting and electron injecting materials may be used in an OLED.
  • Non-limiting examples of the materials that may be used in an OLED in combination with materials disclosed herein are listed in Table 1 below. Table 1 lists non-limiting classes of materials, non-limiting examples of compounds for each class, and references that disclose the materials. TABLE 1 MATERIAL EXAMPLES OF MATERIAL PUBLICATIONS Hole injection materials Phthalocyanine and porphryin compounds Appl. Phys. Lett. 69, 2160 (1996 ) Starburst triarylamines J. Lumin.
  • step 2 The reactor contents from step 2 were cooled to anmbient. 2,4-pentanedione (14.0g 140 mmol) and sodium carbonate (30.0g, 280mmol) were added to the reactor. The reaction mixture was stirred at ambient for 24h. 5g of celite and 500mL of dichloromethane was added to the reaction mixture to dissolve the product. The mixture was then filtered through a bed of celite. The filtrate was then passed through a through a silica/alumina plug and washed with dichloromethane. The clarified solution was then filtered through GF/F filter paper the filtrate was heated to remove most of the dichloromethane.
  • N,N dimethylformamide (DMF) (1L) and potassium tert-butoxide(135.0g 1.2mol) were heated to 50C under nitrogen.
  • Methyl 3-methylbutanoate (86.0g, 0.75mol) was added dropwise from a dropping funnel followed by a solution of 4-methylpentane-2-one(50g, 1mol ) in 100mL DMF.
  • the progress of the reacrtion ws monitored by GC.
  • the reaction was completed, the mixture was cooled to ambient and slowly neutralized with 20% H2SO4 solution. Water (300mL) was added and two layers formed. The layer containing the 2,8-dimethylnonane-4,6-dione was purified using vacuum distillation to give 40g of a pink oil (43% yield)
  • step 4 The reactor contents from step 4 were cooled to anmbient. 2,4-pentanedione (14.0g 140 mmol) and sodium carbonate (30.0g, 280mmol) were added to the reactor. The reaction mixture was stirred at ambient for 24h. 5g of celite and 500mL of dichloromethane was added to the reaction mixture to dissolve the product. The mixture was then filtered through a bed of celite. The filtrate was then passed through a through a silica/alumina plug and washed with dichloromethane. The clarified solution was then filtered through GF/F filter paper the filtrate was heated to remove most of the dichloromethane.
  • 2,8-dimethylnonane-4,6-dione (10.0g, 5.4mmol), potassium tert butoxide (7.0g, 6.5mmol) and 150mL of anhydrous THF was charged in a 3neck 250mL dry round bottom flask. The reaction mixture was stirred under an atmosphere of nitrogen at ambient for 1h. Iodomethane (15g, 105mmol) was added to the reaction mixture via a needle and syringe. The reaction mixture was continued to stir at ambient for a further 4h. The reaction was monitored by GC. The reaction was quenched with 100mL of water and acidified using 1M hydrochloric acid.
  • Dichlorobridged Iridium dimer from step 2 (1.0g, 0.7 mmol), 10 mol eq 2,5,8-trimethylnonane-4,6-dione (1.4g,), 20 mol eq of Na 2 CO 3 (2.0g) and 25 mL of 2-ethoxyethanol were placed in a 250 mL round bottom flask. The reaction mixture was stirred at ambient for 24 hours. 1 g of celite and 100mL of dichloromethane was added to the reaction mixture to dissolve the product. The mixture was then filtered through a bed of celite. The filtrate was then passed through a through a silica/alumina plug and washed with dichloromethane.
  • N-(4-chlorophenylethyl)benzamide (15g, 52mmol), isobutylboronic acid (10.6g, 104mmol), Pd 2 (dba) 3 (1mol%), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (4 mol%), potassium phosphate monohydrate(22.0g 212mmol) 200ml of toluene was charged in a 250mL round bottom flask. Nitrogen was bubbled through the reaction mixture for 20 minutes and heated to reflux for 18h overnight. The reaction mixture was allowed to cool to ambient temperature and the crude product was purified by column chromatography using 2% ethyl acetate in hexanes as solvent. 15g of desired product was obtained (93%yield).
  • N-(4-p-isobutylphenylethyl)benzamide (15.0g), phosphorous pentoxide (50g) phosphorous oxychloride 50mL and xylenes (160mL) was refluxed for 3 h in a 1L round bottom flask. After the reaction mixture was allowed to cool to room temperature, the solvent was decanted and ice was slowly added to the solid in the bottom of the flask. The water-residue mixture was made weakly alkaline with 50% NaOH and the product was extracted with toluene. The organic layer was washed with water and dried over anhydrous MgSO 4 . The solvent was evaporated to give 12.4g of crude product (88% yield) which was used without further purification.
  • N-(4-p-isopropylphenylethyl)benzamide (7.5g) in 80mL xylenes was refluxed for 3 hrs together with 25g phosphorous pentoxide and 25mL phosphorous oxychloride. After cooling, the solvent was decanted and ice was slowly added to the solid in the bottom of the flask. The water-residue mixture was made weakly alkaline with 50% NaOH and the product was extracted with toluene. The organic layer was washed with water and dried over anhydrousMgSO 4 . The solvent was removed under vacuum to give 6.2g of crude product which was used without further purification.
  • Dichlorobridged Iridium dimer from step 2 (1.3g, 0.9 mmol), 10 mol eq 2,8-dimethylnonane-4,6-dione (1.6g,), 20 mol eq of Na 2 CO 3 (2.5g) and 25 mL of 2-ethoxyethanol were placed in a 250 mL round bottom flask. The reaction mixture was stirred at ambient for 24 hours. 2g of celite and 200mL of dichloromethane was added to the reaction mixture to dissolve the product. The mixture was then filtered through a bed of celite. The filtrate was then passed through a through a silica/alumina plug and washed with dichloromethane.
  • 2-amino-4-clorobenzoic acid (42.8g, 0.25mol) was dissolved in 200mL of anhydrous THF and cooled in an ice-water bath. To the solution was added lithium aluminum hydride chips(11.76g, 0.31mol). The resulting mixture was stirred at room temperature for 8 hours. 12g of water was added, and then 12g 15% NaOH. 36g of water was then added. The slurry was stirred at room temperature for 30min. The slurry was filtered. The solid was washed with ethyl acetate. The liquid was combined and the solvent was evaporated. The crude material was used for next step without purification.
  • Compound 9 can be synthesized using the same procedure as outlined for invention compound 7. In this case the dichlorobridged iridium dimer that is formed should be cleaved with 2,4-pentane dione to afford the product.
  • Compound 10 can be synthesized using the same procedure as outlined for invention compound 6. In this case the dichlorobridged iridium dimer that is formed should be cleaved with 2,4-pentane dione to afford the product.
  • All device examples were fabricated by high vacuum ( ⁇ 10 -7 Torr) thermal evaporation.
  • the anode electrode is 1200 ⁇ of indium tin oxide (ITO).
  • the cathode consisted of 10 ⁇ of LiF followed by 1000 ⁇ of Al. All devices were encapsulated with a glass lid sealed with an epoxy resin in a nitrogen glove box ( ⁇ 1 ppm of H 2 O and O 2 ) immediately after fabrication, and a moisture getter was incorporated inside the package.
  • HIL hole injection layer
  • a-NPD 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl
  • HTL hole transporting later
  • BAlq doped with 8-12% of the inventive compound as the emissive layer
  • Alq 3 tris-8-hydroxyquinoline aluminum
  • Comparative Examples 1 and 2 were fabricated similarly to the Device Examples, except that Ir(3-Mepq) 2 (acac) or Ir(piq) 2 (acac) was used as the emissive dopant.
  • the Device Examples containing inventive compounds show similar or higher device efficiency and lifetime and also extremely narrow emission spectra versus the Comparative Examples containing Ir(3-Mepq) 2 (acac) or Ir(piq) 2 (acac).
  • the LE and EQE of Example 3 are 21.1 cd/A and 18.2% respectively, at CIE of (0.662, 0.335).
  • the LE and EQE of Example 4 are 18.7 cd/A and 11.4% respectively, at CIE of (0.666, 0.331).
  • the Full Width Half Max (FWHM) of the EL for examples 3, 4, 6 and 7 are 59, 61, 55 and 55nm respectively. These are by far narrower than the EL measured for Comparative Examples 1 and 2 with FWHM 94 and 84nm, respectively.
  • Device Examples 6 and 7 have the narrowest FWHM of any red iridium complex reported to date. Therefore, the inventive compounds may be advantageously used in devices to improve efficiency, stability and luminescence.
  • the sublimation temperatures using the branched diketone ligand, for example, Compounds 3, 6 and 7, are also quite low which are well suited for long term thermal evaporation required in manufacturing.
  • the 70°C lifetime comparison shows that Device Example 8 is more stable than both Comparative Example I and 2. Therefore, the inventive compounds may be advantageously used in devices to improve device lifetime.

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Claims (15)

  1. Eine Verbindung ausgewählt aus der Gruppe bestehend aus:
    Figure imgb0199
    Figure imgb0200
    Figure imgb0201
    Figure imgb0202
    Figure imgb0203
  2. Die Verbindung nach Anspruch 1, wobei die Verbindung ausgewählt ist aus der Gruppe bestehend aus:
    Figure imgb0204
    Figure imgb0205
  3. Die Verbindung nach Anspruch 1, wobei die Verbindung ausgewählt ist aus der Gruppe bestehend aus:
    Figure imgb0206
    Figure imgb0207
    Figure imgb0208
    Figure imgb0209
  4. Die Verbindung nach Anspruch 1, wobei die Verbindung ausgewählt ist aus der Gruppe bestehend aus:
    Figure imgb0210
    Figure imgb0211
  5. Eine organische Licht emittierende Vorrichtung (100; 200) umfassend:
    eine Anode (115; 260);
    eine Kathode (160; 215); und
    eine organische Schicht angeordnet zwischen der Anode (115; 260) und der Kathode (160; 215), die organische Schicht ferner umfassend eine Verbindung ausgewählt aus der Gruppe bestehend aus:
    Figure imgb0212
    Figure imgb0213
    Figure imgb0214
    Figure imgb0215
    Figure imgb0216
  6. Die Vorrichtung nach Anspruch 5, wobei die Verbindung ausgewählt ist aus der Gruppe bestehend aus:
    Figure imgb0217
    Figure imgb0218
  7. Die Vorrichtung nach Anspruch 5, wobei die Verbindung ausgewählt ist aus der Gruppe bestehend aus:
    Figure imgb0219
    Figure imgb0220
    Figure imgb0221
    Figure imgb0222
  8. Die Vorrichtung nach Anspruch 5, wobei die Verbindung ausgewählt ist aus der Gruppe bestehend aus:
    Figure imgb0223
    Figure imgb0224
  9. Die Vorrichtung nach Anspruch 5, wobei die organische Schicht eine emittierende Schicht (135; 220) umfassend die Verbindung und einen Wirt ist.
  10. Die Vorrichtung nach Anspruch 9, wobei die Verbindung das emittierende Material ist.
  11. Die Vorrichtung nach Anspruch 9, wobei der Wirt ein Metallkoordinationskomplex ist.
  12. Ein Konsumentenprodukt umfassend eine Vorrichtung, die Vorrichtung ferner umfassend:
    eine Anode;
    eine Kathode; und
    eine organische Schicht, angeordnet zwischen der Anode und der Kathode, wobei die organische Schicht ferner eine Verbindung wie in Anspruch 1 definiert umfasst.
  13. Eine metallorganische Verbindung enthaltend eine Struktur ausgewählt aus der Gruppe bestehend aus:
    Figure imgb0225
    Figure imgb0226
     wobei M ein Metall mit einer Atomzahl von mehr als 40 ist.
  14. Die Verbindung nach Anspruch 13, wobei M für Ir steht.
  15. Die Verbindung nach Anspruch 14, wobei die Verbindung ein phosphoreszentes Material ist.
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TW201022209A (en) 2010-06-16
TW201516035A (zh) 2015-05-01
JP6581169B2 (ja) 2019-09-25
CN103539821B (zh) 2017-04-19
JP2018044001A (ja) 2018-03-22
US20150255734A1 (en) 2015-09-10
EP2329541B1 (de) 2015-10-28
CN103539821A (zh) 2014-01-29
KR101974294B1 (ko) 2019-04-30
EP2999021A1 (de) 2016-03-23
TWI555734B (zh) 2016-11-01
KR20160131127A (ko) 2016-11-15
KR20110074538A (ko) 2011-06-30
WO2010033550A1 (en) 2010-03-25
EP2329541A1 (de) 2011-06-08
JP2016102124A (ja) 2016-06-02
JP5878371B2 (ja) 2016-03-08
JP6262190B2 (ja) 2018-01-17
US10084143B2 (en) 2018-09-25
JP2015212297A (ja) 2015-11-26
US20100090591A1 (en) 2010-04-15
KR101649768B1 (ko) 2016-08-19
TWI482756B (zh) 2015-05-01
EP3404736A1 (de) 2018-11-21
CN102187491B (zh) 2013-09-18
EP3404736B1 (de) 2019-12-04
US9034483B2 (en) 2015-05-19
KR20170086673A (ko) 2017-07-26
CN102187491A (zh) 2011-09-14
KR20160005137A (ko) 2016-01-13
JP2012503043A (ja) 2012-02-02

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